U.S. Pat. Nos. 5,364,831, and 6,197,728, disclose herbicidal compounds of the formula:
wherein X represents a halogen atom; R includes —C(═O)R1 where R1 represents various substituted alkoxy radicals, —SR3 radicals, and —NHR4 radicals where R4 is a C1-4 alkoxycarbonylalkyl, hydroxy alkyl, phenyl, C1-4 alkoxy alkyl or di C1-4 alkyl amino groups.
U.S. Pat. No. 4,629,493, discloses herbicidal compounds of the formula:
wherein A is —CH— or —N—; X is a halogen; n is 0,1, or 2; R1 is hydrogen or a lower alkyl group; and R2 is —OH, —Oalkyl, —OM (inorganic or organic salt), —NR3R4 where R3 and R4 respectively represent a hydrogen atom or a lower alkyl group. One of these compounds is currently sold commercially for the control of annual and perennial grass weeds in broadleaf crops. This compound has the following formula:

Corbett et. al., Investigational New Drugs, 16, 129-139 (1998), evaluated a series of quinoxaline compounds for activity against solid tumors in mice. The following compound
(herein after referred to as XK469) was reported to have broad activity against transplantable mouse tumors. The compound was also reported to have a relatively low potency, and to produce several undesirable side effects, including in vivo toxicity, e.g., paralytic ileus, GI-epithelial damage, marrow toxicity, neuromuscular toxicity, and weight loss.
Hazeldine et al., J. Med. Chem., 2001, 44, 1758-1776, disclose anti-tumor compounds of the formula:
wherein, for example, W can be H or Cl; X can be H, Cl, F, or NO2; Y can be H, F, Cl, Br, I, methoxy or —N3; Z can be H, Cl, or methoxy; and R can be OH, alkoxy, or NR′R″, where R′ and R″ are H, methyl, NH2 or OH, see Table 5 therein.
Hazeldine et al., J. Med. Chem., 2002, 45, 3130, disclose bioisostere and cogener compounds of anti-tumor compound (XK469).
Copending provisional application U.S. Ser. No. 60/309,144, filed Jul. 7, 2001, now PCT application PCT/US02/24442, entitled “Anti-tumor Agents” discloses a compound of the formula:
wherein Y is F, Cl, Br, methyl, or methoxy; or a pharmaceutically acceptable salt thereof.
There is currently a need for additional anti-tumor agents.